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Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.

Photo gallery for Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.

Serene 40x20 heated saltwater pool behind the guest cottage
Relax or enjoy food and drinks by the pool
Fully fenced in pool area
Outdoor dining table by the pool and hammock by the stream
Private outdoor shower by the pool

Reviews

10 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 4185.8 sq m

Popular amenities

  • Dryer
  • Fireplace
  • Washer
  • Kitchen
  • Hot tub
  • Barbecue grill

Explore the area

Map
Bearsville, NY
  • Woodstock Music Shop
    ‪4 min drive‬
  • Woodstock Golf Club
    ‪5 min drive‬
  • Overlook Mountain Trailhead
    ‪12 min drive‬
  • Hudson, NY (HCC-Columbia County)
    ‪52 min drive‬

Rooms & beds

4 bedrooms (sleeps 4)

Bedroom Guest House

1 King Bed

Guest bedroom main house

2 Single Beds

Living room guest house

1 Double Sofa Bed

Main Bedroom main house

1 Queen Bed

2 bathrooms

Bathroom guest house

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo

Bathroom main house

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden
Dining area

About this property

Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.

The Bearsville Retreat is a secluded bucolic compound nestled in the trees of Bearsville, a quarter mile from the gourmet marketplace The Cub and the historic Bearsville Theater, and just two miles (5 min drive) to Woodstock's town center. The property consists of two charming cottages, freestanding office, heated saltwater pool (there is an additional fee to heat the pool), luxurious hot tub, fire pit, and a children's play structure. Pastoral and mountain views abound. Come relax, recharge, and enjoy the natural beauty of the Catskills.

Located in Bearsville, a hamlet of Woodstock, the serene two-acre property is tucked away from the road, with beautiful mountain views, providing a postcard-perfect backdrop to wake up to every morning, while also close to everything. Spend your afternoons swimming in the heated saltwater pool, relax in the hot tub, or lounge in a hammock in the apple orchard while the kids swing and play in the club house. Pass your evenings barbecuing and dining alfresco on the bluestone patio, playing charades in the game room, or roasting marshmallows in the fire pit. Located within the historic township of Woodstock, with it’s charming boutiques, farm-to-table restaurants, and rich history of music and art, The Bearsville Retreat is the perfect spot to enjoy all that the Catskills have to offer.

THE MAIN HOUSE has two bedrooms: The primary bedroom has a queen bed, and the second bedroom has two twin beds — both bedrooms are cozy and comfortable with designer furniture, premium bedding, and new skylights. The brand-new kitchen is fully stocked with microwave, coffee maker, and everything you need to cook for family or guests. The bathroom features both walk-in shower and deep soaking tub — a relaxing treat at the end of a long day of hiking or skiing. The stylishly-decorated living room has a wood burning fireplace and plenty of comfy seating, Apple TV, bluetooth stereo/record player, and wifi that extends across the property. The game room, which is stocked with board games, puzzles, art books and an antique chess/backgammon table, leads out to a sunny bluestone patio with a twelve-person al fresco dining table and barbecue. The wood-paneled dining room is a cozy space with the feel of an old fashioned captain's stateroom, an ideal spot for both quiet breakfasts and lively dinner parties.

THE GUEST HOUSE features open floor plan with a loft-like, sun-filled living room with a wall of windows facing onto the pool. There is wifi throughout the house, as well as a smart TV/Blue ray and record player. There is a mini library filled with books and DVDs which can be enjoyed on the sofa in front of the pot-bellied stove. The chef’s kitchen is fully equipped with new appliances, a marble-topped island, and plenty of counter space for preparing meals. The spacious dining area comfortably seats six. The bedroom has a luxurious king sized bed with upholstered headboard, and plenty of natural light from windows facing out to the pool. The bathroom features a deep soaking tub and skylight, perfect for relaxing and looking up at the stars. The sofa in the living room converts into a queen bed for extra sleeping space (please let us know ahead of time if you want this bed made up before you arrive).

THE GROUNDS' beautifully maintained sprawling lawns are picturesque. The 20' X 40' heated saltwater pool (additional heating fee), outdoor shower, and brand new hot tub are privately situated in the back yard, while the front yard features an apple orchard, pastural views of the historic neighboring farm, a fire pit, and a 'Brad's Barns Expedition' children's swing-set, with play structure, and club house.

THE OFFICE is a freestanding building located behind the main house. It is equipped with a desk, plush couch, and hardwired ethernet. It is private and comfortable, making work away from home a breeze.

See you soon!

Property manager

Erica O'Neill
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
No more than 8 people total including the guests
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Pets

Pets allowed: dogs (limit 1 total)
Please message me to get permission first
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Smoking

Smoking is not permitted
There is a fee for well-behaved dogs.
Guests staying long term are required to have the house cleaned at least every 2 weeks (using our cleaner)
All garbage and recycling to be properly bagged and brought to the garbage bins in the driveway when you check out

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: no more than 8 people total including the guests
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
Property Registration Number 23H-068

We should mention

A car is recommended for transport to and from this property

About the area

Bearsville

Located in Bearsville, this cottage is in a rural area. SweetHeart Gallery and James Cox Gallery are cultural highlights, and travellers looking to shop may want to visit Hudson Valley Mall and Vinnie's Farm Market. Travelling with kids? Consider Woodstock Music Shop, or check out an event or a game at Dietz Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Bearsville, NY

What's nearby

  • Woodstock Music Shop - 4 min drive - 4.0 km
  • Byrdcliffe Barn - 5 min drive - 4.5 km
  • Woodstock Golf Club - 5 min drive - 4.7 km
  • Overlook Mountain Trailhead - 12 min drive - 8.1 km
  • Karma Triyana Dharmachakra Monastery - 12 min drive - 8.1 km

Getting around

  • Rhinecliff Station - 31 min drive
  • Hudson, NY (HCC-Columbia County) - 52 min drive

Restaurants

  • ‪Olive's Country Store & Cafe - ‬16 min drive
  • ‪Colony - ‬4 min drive
  • ‪Bread Alone - ‬4 min drive
  • ‪Good Night - ‬4 min drive
  • ‪Tinker Street Tavern - ‬11 min walk

Frequently asked questions

Does Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting. have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting. pet-friendly?

Yes, this property allows dogs (limit 1 total).

What time is check-in at Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.?

Check-in begins at 3:00 PM.

What time is check-out at Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.?

Checkout is at 10:00 AM.

Where is Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting. located?

This family-friendly Bearsville cottage is located in a rural location, within 2 mi (3 km) of Catskill State Park and Woodstock Dog Park. Woodstock Music Shop and Woodstock Public Library are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 65 out of 67 reviews
Rating 8 - Good. 2 out of 67 reviews
Rating 6 - Okay. 0 out of 67 reviews
Rating 4 - Poor. 0 out of 67 reviews
Rating 2 - Terrible. 0 out of 67 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Peter K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Upstate

Erica went above and beyond to make sure we were comfortable during our stay. The house is beautiful nd we can’t wait to come back.
Stayed 3 nights in Feb 2025

10/10 Excellent

Elana A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

The property is beautiful, clean, and charming. Right next to a picturesque farm with bulls, goats, and chickens, and just 5 mins from town. We will definitely come back to this lovely place
Stayed 2 nights in Nov 2024

10/10 Excellent

Dana Claire D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Place

The Bearsville retreat was amazing. Its location was perfect, the accommodations were spotless and the owner was super helpful and responded quickly. We left today and already rebooked for next year.
Stayed 3 nights in Aug 2024

10/10 Excellent

Jacqueline C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enchanted cottage

Lovely property
Stayed 6 nights in Jul 2024

10/10 Excellent

Katie D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible property in a great location!

My group and I had such a fantastic stay! The two cottages were comfortable and cozy and the pool was beautiful. We were close to town and other amenities. I would highly recommend a stay here, my group hopes to come back soon!
Stayed 3 nights in Jun 2024

10/10 Excellent

Debra & Jake F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls trip

Clean, comfortable, & well appointed space for our Woodstock weekend! Loved it!
Stayed 3 nights in Aug 2024

10/10 Excellent

Adam T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A wonderful space to catch up

I had a lovely time celebrating my upcoming wedding with my closest friends, and this property made it all the more special and fun. Great location, well maintained, and just a great time. Erica was very communicative and helpful.
Stayed 2 nights in Sep 2024

10/10 Excellent

Ruth L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Stay

House was amazing and it was so easy and organized. We will be back!
Stayed 2 nights in Jun 2024

10/10 Excellent

Katherine H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy

It rained most for most of our stay, so it was quite cozy staying indoors. The fireplace and turntable were a plus!
Stayed 3 nights in Apr 2024

10/10 Excellent

Michael G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A perfect getaway

We had an absolutely wonderful time at the property. The house and the grounds were as advertised. The separate cottages and separate office workspace offered privacy for the different family members in our party. Everything was clean and well maintained. The property definitely retained the rustic feel of upstate NY, but recent upgrades were evident and all appliances and utilities worked very well. The property manager was extremely responsive and addressed any questions quickly. Our kids enjoyed the pool and the playset and seeing the animals on the farm next door. Location could not be better - so close to Woodstock town center and everything else Hudson Valley has to offer. We are excited to return soon.
Stayed 8 nights in Aug 2024

10/10 Excellent

Kimberly M., FOREST HILLS

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy Winter Getaway

This property has lots of charm and a great location too. Looking out the large picture window onto the snow-capped mature trees by the cozy fire was a real treat. Clean and comfortable it has all you need for a great time away. Sarah was an incredible host and went above and beyond!
Stayed 2 nights in Feb 2021

10/10 Excellent

Dori B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

tranquil paradise

I stayed for a month using both houses. The property is well equipped in a lovely setting with a fantastic pool. The manager responded quickly during normal hours. Great all around.
Stayed 29 nights in Jul 2023

10/10 Excellent

Vicky O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing Stay

We really enjoyed our stay at the cottages. The setup was great for two families as we each had our own cottage, so privacy when we needed it but also great communal areas to come together for meals and fun. We have two young kids, age 2 and 4 and they loved the playground area and seeing the deer and chipmunks around the property. The pool was a really good size and temperature. Wish we could have used it more but some wasps decided to build their nest on the back of one of the loungers! Erica was really responsive about it and did her best to rectify the issue quickly. The place is very convenient for exploring Woodstock and Bearsville and we had everything we needed for a relaxing stay, would definitely go back. Thanks Erica!
Stayed 3 nights in Jun 2024

10/10 Excellent

Lara R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Holiday escape

My wife and I, and our friends, return to this property again and again for the past 15-20 years. Now with new owners, we appreciate the upgrades as we haven’t been for a few years now. Property is rural, next to a farm and visited daily by rabbits, deer, owls, and other wildlife. House is cozy, with a superb fireplace. Separate cottage is good for a couple or if someone needs a place to work from home. Clean, simple, stocked with cooking supplies, books, TV, so you can settle in and enjoy the property. Brand new hot tub, which we didn’t actually use as it was very cold during our stay, but it was serviced and looks perfect. Pool closed for winter but we’ve enjoyed it in past years - fantastic. Two minute drive to Woodstock. Very convenient. Lots of local restaurant recs in house handbook. Small-dog friendly (at owner discretion) is a huge plus. Would be magnificent if a portion of yard could be completely fenced in to allow for carefree romping for free-roaming dogs that like to chase those bunnies and deer :) One unforeseen issue due to subzero temps was handled promptly by attentive property manager, who is local and available 24/7 for any needs. Highly recommend this property for friends or families looking to get away, but with mod cons of Woodstock very nearby. You’ll make lots of new, cherished memories.
Stayed 9 nights in Dec 2024

10/10 Excellent

Alison W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Woodstock stay!

We loved these cottages! We were a group of 5 with kids, parent, and grandparents. The two-cottage set up was a great arrangement for us, giving the grandparents some privacy, and the pool and hot tub provided lots of entertainment for the kids. The houses were well appointed with lovely furnishings and plenty of supplies/equipment for cooking and towels for the pool. Location was another of our favorite features- the houses were on a beautiful piece of land beside a small farm, and just a five or so minute drive from the main part of Woodstock. The one suggestion for improvement would be to some of the outdoor areas and furniture, which could use a power wash or, in some cases, to be replaced. Some shrubs could use cutting back, like at the end of the driveway and in the pool area, but obviously it’s tough to maintain such an extensive property! We would absolutely stay here again.
Stayed 7 nights in Jun 2024

10/10 Excellent

Ayesah H., New York City

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely wonderful!

We absolutely loved our stay here, not only was it beautiful but it was so cozy. Town was extremely close by, as well as hiking and other acgivities. There was wildlife all around, beautiful deer to view on the lawn every morning and afternoon, and the view of the pool in the afternoon is a bird watchers dream. It felt like complete country living. We wished we had stayed longer! Our pup also enjoyed himself to the absolute fullest, having a fenced in yard was so amazing for him, he was able to run his heart out and we never had to worry! I was so pleased to be able to reach out whenever we needed something and got an answer right away from the property manager. We hope to stay here again!
Stayed 5 nights in Aug 2023

10/10 Excellent

Lucy D., Manhasset, USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Weekend Break

We wanted the chance to relax in different surroundings (surprising how working from home for most of the year can make you stir crazy!) and get our Christmas season off to a good start, and boy did the house fit the bill. We stayed in the main house at Bearsville and it is wonderful; cozy, clean and fully stocked. We loved the curtained in main bedroom - a modern twist on a four poster. And the Christmas lights round the fireplace were a delightful touch. The location is also great - just a few minutes drive into town for shopping and eating. All in all a wonderful retreat and perfect place to recharge. Oh, and the dog loved it too! Thank you!!
Stayed 2 nights in Dec 2020

10/10 Excellent

Lauren F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Pup Getaway

We cant say enough nice things about this property. Started off with very easy and informative communication with the owner. The property itself checks all the boxes for a wonderful weekend away, especially for those with dogs. The entire property is completely fenced so the dogs could roam free without a worry. We weren't able to use the pool as it was April, but the hot tub was lovely. We also used the grill quite a bit to cook very easily. The houses are updated in the most important places, kitchen and bathroom. While the rest of the house has such charm and character. The open windows make the space relaxing and inviting. We had a fire inside every night while enjoying a night cap and chat. The location is extremely convenient to nearby shops, restaurants of Woodstock and Bearsville. We wish we would have stayed longer, so we will be back, as long as we can get a booking. Thanks again Sarah.
Stayed 3 nights in Apr 2021

8/10 Good

lisa A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place after a tough start

Our vacation started out stressful as our dog ingested poison from a rodent trap. We had to go to an all night vet and were up most of the night. Our dog is fine thank goodness! The home owner was really helpful. One the phone with us in the middle of the night, helping with the vet and vet bills. I could tell she really cared and did all she could for us. I could not have asked for her to be more ready to help us in any way. She has made a beautiful, peaceful place. Everything you need is in the kitchen, including high quality knives, which I always appreciate. The property is quiet and private. The views across the farm are beautiful. She has a house book with a lot of instructions, which helps with answering most of your questions but she is very available if questions come up. There are quite a few house rules, but that is how she keeps the house so nice. She also has great suggestions in the book for local activities and restaurants, some you would not find in a guide book. All and all, a thoughtfully run place. I would suggest two things. I wished there was more light at night. The light bulbs are low wattage and I would have wanted it brighter. I would also suggest a large bread box to put food that really shouldn't go into the fridge as she wants no food left out. So, you would think that after the scare with our beloved family member we would have left with a bad feeling, but we did not. Sarah was great and so was her place. I would recommend it to my friends and would return myself.
Stayed 5 nights in May 2021

10/10 Excellent

Tom S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stayed 3 nights in Oct 2024

10/10 Excellent

pete g.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Weekend Getaway

We came for a long weekend (2 couples). The main house has two beds, very comfortable for the four of us. The guest house which we didn’t need to use would have been great for another couple or even a family. Plenty of space all around. The fireplace was great and stocked with plenty of wood. To start, Sarah was extremely responsive and accommodating with us regarding checkin and out time. She has a very detailed list of things to do around the area and a house manual. Some reviews noted a bunch of “rules”, but all seemed totally reasonable to us and we found the information very helpful. The house had a hot tub which we used and a beautiful pool which we did not given it was October. I could see spending a ton of time in the pool in spring/summer - it was really nice. The house was close to the town so getting meals was easy. Also the house is close to Overlook Mountain (and others) and we went on a nice hike (about 4 hours round trip). Overall, it was a fantastic weekend getaway and we hope to come back soon.
Stayed 2 nights in Oct 2021

8/10 Good

Erin G.

Liked: Cleanliness, check-in, communication, location

Beautiful property w/ many rules

Our family very much enjoyed our stay at this property. It was peaceful and tucked away. However, I was overwhelmed with the amount of communication that the owner wanted, and with the threat of extra charges in how the property was used. We ended up using the property far less than I had originally anticipated due to the extensive rule book and list of activities that would incur further charges. Furthermore, the description that the pool was heated was inaccurate and should have read that the pool ‘has the ability to be heated at great additional cost’. While we made a fun week of it, this was by far the most stressful booking I’ve ever had through VRBO, and I had the impression that the owner wasn’t actually interested in this being used as a rental property.
Stayed 7 nights in Aug 2021

10/10 Excellent

april h., Rehoboth Beach, DE

Liked: Cleanliness, check-in, communication, location, listing accuracy

Close to town

Close to town and the Cub Market, private, quiet
Stayed 7 nights in Apr 2021

10/10 Excellent

Maria M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Much Needed Retreat

The property was perfect for a quick little getaway. Can’t wait to book it again. :)
Stayed 3 nights in Apr 2021

10/10 Excellent

Thomas C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway

Perfect little getaway with the wife and kids. Property is beautiful and peaceful just a great experience from booking to check out!!
Stayed 2 nights in Apr 2021

About the host

Hosted by Erica O'Neill

Host profile image
A painter who has long loved the Woodstock area.

Why they chose this property

Charm Charm Charm, Built by the neighboring farmer's family in 1930 for an emigre family from Germany. It has a woodsy feel with charming little details. When we first saw it it was the setting that grabbed us, it's not grand but super relaxed and now a little lux with the new bathrooms and kitchens and the addition of the new hot tub and heated saline pool. The Hamlet of Bearsville has green hills and dark starry nights.
Come and rejuvenate yourself in the relaxing compound, set in landscaped grounds surrounded by flowering apple and magnolia trees.

What makes this property unique

You are in the country with all delicious benefits, from the farm next door where you can walk over in the morning and buy your happy eggs, to outdoorsy activities like swimming holes, hiking, tubing & trout fishing, yet close to everything you would need to have a relaxing time, with art galleries, Zagat rated restaurants, a cute little village for a stroll and some shopping and the relaxed atmosphere of a cosmopolitan environment in this historic arts community walkable to cocktails at the Bearsville Cafe compound.

Languages:

English

Premier Host

They consistently provide great experiences for their guests